Title: Book the Best Siesta Isle WINERY Hotels in 2025 | Expedia.ca [Vacation Rentals in Fort Myers Beach](https://expedia.ca/Fort-Myers-Beach-Vacation-Rentals.d7194.Travel-Guide-VacationRentals)[Flights to Fort Myers Beach](https://expedia.ca/Cheap-Flights-To-Fort-Myers-Beach.d7194.Travel-Guide-Flights)[Things to do in Fort Myers Beach](https://expedia.ca/Things-To-Do-In-Fort-Myers-Beach.d7194.Travel-Guide-Activities)[Siesta Isle Car Rentals](https://expedia.ca/Car-Rentals-In-Siesta-Isle.d553248635976473609.Car-Rental-Guide)[Siesta Isle Vacations](https://expedia.ca/Siesta-Isle.d553248635976473609.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/9/7643f75a1eaf3da6ab0ea44cfc4ff082.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Siesta Isle, FL from CA $419 ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Siesta Isle Winery Hotels Tonight [Oct 16 - Oct 17](https://www.expedia.ca/Hotel-Search?regionId=553248635976473609&startDate=2025-10-16&endDate=2025-10-17&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 17 - Oct 18](https://www.expedia.ca/Hotel-Search?regionId=553248635976473609&startDate=2025-10-17&endDate=2025-10-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976473609&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976473609&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Siesta Isle Winery Hotels ![A heated pool](https://images.trvl-media.com/lodging/112000000/111930000/111924400/111924394/c0a1da9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/112000000/111930000/111924400/111924394/823ef621.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, printers](https://images.trvl-media.com/lodging/112000000/111930000/111924400/111924394/4dccce44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/112000000/111930000/111924400/111924394/d21e3f98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront Condo with Pool & Boat Slip Caloosahatchee 10/10 Exceptional (1) "Nice place with a lot of fun activities for the kids. " CA $122 CA $479 total includes taxes & fees Oct 17 - Oct 18 [](https://www.expedia.ca/Cape-Coral-Hotels-E-SeatuitSwimFishBoayKayakRelax-Vacay-E.h111924394.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/72000000/71520000/71510500/71510479/7993b11f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, music library, video library](https://images.trvl-media.com/lodging/72000000/71520000/71510500/71510479/50a2ebbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/72000000/71520000/71510500/71510479/43ad42c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/72000000/71520000/71510500/71510479/d97c5288.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### RARE FIND COASTAL COZY BRIGHT 2BR 2BATH HOME! 10MINS AWAY TO THE BEACH! Hancock 10/10 Exceptional (11) "We had such a great time staying here! The place was super cute and really clean, and the host was so nice and attentive. The outdoor area had a really cool vibe perfect for hanging out and relaxing. There was also plenty of parking, which made things easy. The little complimentary touches were really thoughtful and appreciated. The whole area felt safe and chill. Overall, just a great spot we’d definitely come back!" CA $120 CA $419 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Cape-Coral-Hotels-Cape-Coastal-Paradise-Apartment.h71510479.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/103000000/102240000/102232800/102232728/bd943b05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/103000000/102240000/102232800/102232728/5ed702ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102240000/102232800/102232728/ed74d17b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/103000000/102240000/102232800/102232728/1451d6c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gulf Access Condo Heated Pool & Dock Caloosahatchee 10/10 Exceptional (24) "The property was very clean and well equipped. Beautiful location on the canal." CA $122 CA $479 total includes taxes & fees Oct 17 - Oct 18 [](https://www.expedia.ca/Cape-Coral-Hotels-Seatuit-Gulf-Access-2Bed2BathB.h102232728.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/103000000/102230000/102222100/102222035/34d2581e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/103000000/102230000/102222100/102222035/cccbbab4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/103000000/102230000/102222100/102222035/8effb523.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102230000/102222100/102222035/d566be44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront Home with Pool & Boat Slip Caloosahatchee 10/10 Exceptional (8) "Property was clean and welcoming. Location was convenient to everything we needed or wanted to do. Was nervous to share the pool area with the other guest in such a small condo but it ended up being perfect." CA $137 CA $569 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Cape-Coral-Hotels-Seatuit-Gulf-Boat-Slip.h102222035.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/106000000/105250000/105241100/105241034/3abae27c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, offices](https://images.trvl-media.com/lodging/106000000/105250000/105241100/105241034/b2a9577b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105250000/105241100/105241034/2e033e49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, offices](https://images.trvl-media.com/lodging/106000000/105250000/105241100/105241034/c41bc781.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sea La Vie Beach House Bonita Shores 9.2/10 Wonderful (5) "This was a great house! Seemed newly renovated; we felt like we were the first guests to stay there! Great proximity to the beach and restaurants. Only thing we missed were oven mits lol" [](https://www.expedia.ca/Bonita-Springs-Hotels-Sea-La-Vie-Beach-House.h105241034.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/35000000/34060000/34058300/34058217/a26692b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34060000/34058300/34058217/c1dc30f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34060000/34058300/34058217/5343b248.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player, books](https://images.trvl-media.com/lodging/35000000/34060000/34058300/34058217/2eee0960.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Perfect home on the canal, Terrace, pool, south facing, WiFi, SW Cape Coral Pelican 10/10 Exceptional (60) "Wonderful house! Everything we needed was there. Would stay again!" CA $204 CA $628 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Cape-Coral-Hotels-Perfect-Home-On-The-Canal.h34058217.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/89000000/88380000/88371400/88371317/23aec766.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, offices](https://images.trvl-media.com/lodging/89000000/88380000/88371400/88371317/96a0e9b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88380000/88371400/88371317/w1200h798x0y0-6ac9c656.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/89000000/88380000/88371400/88371317/a4583a76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### \* The 97th \* Naples Park 9.6/10 Exceptional (12) "MY wife & I enjoyed our stay here. Very relaxing home!" CA $267 CA $955 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Naples-Hotels-The-97th.h88371317.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/76000000/75960000/75957100/75957061/b9244ebe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75960000/75957100/75957061/0f293da9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/76000000/75960000/75957100/75957061/c2c47551.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75960000/75957100/75957061/15eb9c4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family Oasis: Waterfront w/ Heated Pool & Game Room! Hancock 10/10 Exceptional (30) "Beautiful home. Extremely clean and comfortable. The host responded right away. The stay there inspired me to get rid of all my clutter in my home. It had everything you’ve ever needed yet there’s absolutely no clutter! The place was amazing. I want to live there so bad. Pool area was perfect. I want to go back - like now!" CA $263 CA $734 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Cape-Coral-Hotels-AMAZING-Dream-GetawaySpacious-Waterfront-Villa-W-Heated-Pool-Spa.h75957061.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/82000000/81880000/81877400/81877351/9df72290.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/82000000/81880000/81877400/81877351/7904a94f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/82000000/81880000/81877400/81877351/a52d4697.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/82000000/81880000/81877400/81877351/57d63415.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### \* The 96 \* Naples Park 9.6/10 Exceptional (12) "Fantastic stay. Clean place, great screened outdoor pool with pool chairs and nice dining area. We had a great stay" CA $298 CA $998 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Naples-Hotels-The-96.h81877351.Hotel-Information) ![Smart TV, books](https://images.trvl-media.com/lodging/101000000/100110000/100101800/100101792/eb59d1bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/101000000/100110000/100101800/100101792/4ff7d54c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/101000000/100110000/100101800/100101792/714ac2d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100110000/100101800/100101792/81a4b7e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Naples Home - Heated Pool, Outdoor TV & Fire Pit Naples Park 10/10 Exceptional (1) "Close to restaurants, beach, golf. Just what we needed" CA $463 CA $1,075 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Naples-Hotels-Newly-Renovated-Naples-Coastal-Comfort.h100101792.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-30&endDate=2025-10-31®ionId=553248635976473609&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Siesta Isle Hotel Reviews ## Explore a world of travel with Expedia - Lodging - More ways to book - [Cheap Hotels in Downtown Fort Myers Beach](https://www.expedia.ca/Downtown-Fort-Myers-Beach-Fort-Myers-Beach-Hotels-Cheap-Hotels.0-n904326898430316544-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Golf Hotels in Downtown Fort Myers Beach](https://www.expedia.ca/Downtown-Fort-Myers-Beach-Fort-Myers-Beach-Hotels-Golf-Hotel.0-n904326898430316544-0-tGolfHotel.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Downtown Fort Myers Beach](https://www.expedia.ca/Downtown-Fort-Myers-Beach-Fort-Myers-Beach-Hotels-Pet-Friendly-Hotel.0-n904326898430316544-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Egmont Key State Park](https://www.expedia.ca/Egmont-Key-State-Park-Hotels-Luxury-Hotel.0-0-d6256666-tLuxuryHotel.Travel-Guide-Filter-Hotels) - 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